Hydrazonoacetic acid amides and the use thereof as pesticides

ABSTRACT

The invention concerns hydrazonoacetic acid amides of general formula (I), a process for producing them, and the use of the said amides as pesticides. In the formula shown, the following meanings apply: A stands for a simple bond or optionally substituted alkylene; Q stands for oxygen or sulphur, R 1  stands for optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl; R 2  stands for hydrogen or optionally substituted alkyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl; R 3  and R 4  are identical or different and each stand for hydrogen or optionally substituted alkyl or cycloalkyl; R 2  and R 3  together with the nitrogen atom to which they are bound form an optionally substituted heterocyclyl ring; R 5  stands for optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl.

This application is a 371 of PCT/EP96/01308, filed Mar. 25, 1996.

The invention relates to novel hydrazonoacetamides, to a process fortheir preparation and to their use as pesticides.

This invention provides novel compound of the general formula (I)##STR1## in which A represents a single bond or optionally substitutedalkylene,

Q represents oxygen or sulphur,

R¹ represents respectively optionally substituted cycloalkyl,cycloalkenyl, aryl or heterocyclyl,

R² represents hydrogen or respectively optionally substituted alkyl,cycloalkyl, cycloalkenyl, aryl or heterocyclyl,

R³ and R⁴ are identical or different and each represents hydrogen orrespectively optionally substituted alkyl or cycloalkyl,

R² and R³ join with the linking nitrogen atom to form an optionallysubstituted heterocyclyl ring,

R⁵ represents respectively optionally substituted cycloalkenyl,cycloalkenyl, aryl or heterocyclyl.

In the definitions, the saturated or unsaturated hydrocarbon chains,such as alkyl, alkanediyl, alkenyl or alkinyl, including when combinedwith hetero atoms, as in alkoxy, alkylthio or alkylamino, are in eachcase straight-chain or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine,preferably fluorine, chlorine or bromine, in particular fluorine orchlorine.

Aryl represents aromatic, mono or polycyclic hydrocarbon rings, such as,for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenylor naphthyl, in particular phenyl.

Heterocyclyl represents saturated or unsaturated and aromaticring-shaped compounds in which at least one ring member is a heteroatom, i.e. an atom other than carbon. If the ring contains more than onehetero atom, these may be identical or different. Preferred hetero atomsare oxygen, nitrogen or sulphur.

Ring-shaped compounds optionally combine with further carbocyclic orheterocyclic, fused or bridged rings to form a polycyclic ring system.Preference is given to mono- or bicyclic ring systems, in particular tomono- or bicyclic aromatic ring systems.

Cycloalkyl represents saturated carbocyclic ring-shaped compounds whichtogether with further carbocyclic, fused or bridged rings optionallyform a polycyclic ring system.

Cycloalkenyl represents carbocyclic ring-shaped compounds which containat least one double bond and which together with further carbocyclic,fused or bridged rings optionally form a polycyclic ring system.

Finally, it was found that the novel hydrazonoacetamides of the generalformula (I) have very strong fungicidal activity.

The compounds according to the invention may be present as mixtures ofdifferent possible isomeric forms, in particular of stereoisomers, suchas, for example, E and Z, threo and erythro, and optical isomers. Whatis described and claimed includes both the E and the Z isomers, and alsothe threo and erythro and the optical isomers and any mixtures of theseisomers.

The invention preferably provides compounds of the formula (I) in which

A represents a single bond or represents alkylene having 1 to 6 carbonatoms which is optionally mono- or polysubstituted by identical ordifferent substituents, the possible substituents preferably beingselected from the list below:

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl,thiocarbamoyl;

respectively straight-chain or branched alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbonatoms; respectively straight-chain or branched alkenyl or alkenyloxyhaving in each case 2 to 6 carbon atoms;

respectively straight-chain or branched halogenoalkoxy,halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonylhaving in each case 1 to 6 carbon atoms and 1 to 13 identical ordifferent halogen atoms;

respectively straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13identical or different halogen atoms;

respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 6 carbonatoms in the individual alkyl moieties;

cycloalkyl having 3 to 6 carbon atoms;

and aryl or heterocyclyl, each of which is optionally mono- orpolysubstituted by identical or different substituents from

halogen, cyano and/or straight-chain or branched alkyl having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkyl having 1 to 4 carbonatoms and 1 to 9 identical or different halogen atoms

and/or straight-chain or branched alkoxy or alkylthio having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkoxy or halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 9 identical or different halogenatoms

and/or respectively doubly attached alkylene or dioxyalkylene having ineach case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different substituents from halogenand/or straight-chain or branched alkyl having 1 to 4 carbon atomsand/or straight-chain or branched halogenoalkyl having 1 to 4 carbonatoms and 1 to 9 identical or different halogen atoms.

Q represents oxygen or sulphur,

R¹ represents aryl, cycloalkyl or cycloalkenyl having 3 to 7 carbonatoms, or heterocyclyl having 3 to 12 ring members, each of which isoptionally mono- or polysubstituted by identical or differentsubstituents, the possible substituents preferably being selected fromthe list below:

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl,thiocarbamoyl; respectively straight-chain or branched alkyl, alkoxy,alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6carbon atoms;

respectively straight-chain or branched alkenyl or alkenyloxy having ineach case 2 to 6 carbon atoms;

respectively straight-chain or branched halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonylhaving in each case 1 to 6 carbon atoms and 1 to 13 identical ordifferent halogen atoms;

respectively straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13identical or different halogen atoms;

respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 8 carbonatoms in the individual alkyl moieties;

respectively doubly attached alkylene or dioxyalkylene having in eachcase 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen and straight-chain or branched alkyl having 1 to 4carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4carbon atoms and 1 to 9 identical or different halogen atoms;

cycloalkyl having 3 to 6 carbon atoms;

and aryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio,heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl,heterocyclylalkyloxy or heterocyclylalkylthio,

each of which is optionally mono- or polysubstituted by identical ordifferent substituents from

halogen, cyano and/or straight-chain or branched alkyl having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkyl having 1 to 4 carbonatoms and 1 to 9 identical or different halogen atoms

and/or straight-chain or branched alkoxy or alkylthio having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkoxy or halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 9 identical or different halogenatoms

and/or respectively doubly attached alkylene or dioxyalkylene having ineach case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen and/or straight-chain or branched alkyl having 1to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms.

R² represents hydrogen or represents alkyl having 1 to 4 carbon atoms orcycloalkyl having 3 to 6 carbon atoms, each of which is optionally mono-or polysubstituted by identical or different substituents from the groupconsisting of halogen, cyano, hydroxyl, amino, C₁ -C₄ -alkoxy, C₁ -C₄-alkylthio, C₁ -C₄ -alkylsulphinyl and C₁ -C₄ -alkylsulphonyl (each ofwhich is optionally substituted by halogen) or represents optionallysubstituted phenyl, the possible substituents being selected from thelist for R¹ above,

R² and R³ join with the linking nitrogen atom to form heterocyclyl whichis in each case optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of halogen, cyano,hydroxyl, amino, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl and C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkyl (each of whichis optionally substituted by halogen),

R³ and R⁴ are identical or different and each represent hydrogen orrepresent alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6carbon atoms, each of which is optionally mono- or polysubstituted byidentical or different substituents from the group consisting ofhalogen, cyano, hydroxyl, amino, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁-C₄ -alkylsulphinyl and C₁ -C₄ 7alkylsulphonyl (each of which isoptionally substituted by halogen),

R⁵ represents aryl, cycloalkyl or cycloalkenyl having 3 to 8 carbonatoms, or heterocyclyl having 3 to 12 ring members, each of which isoptionally mono- or polysubstituted by identical or differentsubstituents, the possible substituents preferably being selected fromthe list below:

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl,thiocarbamoyl,

respectively straight-chain or branched alkyl, alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbonatoms;

respectively straight-chain or branched alkenyl or alkenyloxy having ineach case 2 to 6 carbon atoms;

respectively straight-chain or branched halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonylhaving in each case 1 to 6 carbon atoms and 1 to 13 identical ordifferent halogen atoms;

respectively straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13identical or different halogen atoms;

respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 6 carbonatoms in the individual alkyl moieties;

respectively doubly attached alkylene or dioxyalkylene having in eachcase 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen and straight-chain or branched alkyl having 1 to 4carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4carbon atoms and 1 to 9 identical or different halogen atoms;

cycloalkyl having 3 to 6 carbon atoms;

and aryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio,heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl,heterocyclylalkyloxy or heterocyclylalkylthio,

each of which is optionally mono- or polysubstituted by identical ordifferent substituents from

halogen, cyano and/or straight-chain or branched alkyl having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkyl having 1 to 4 carbonatoms and 1 to 9 identical or different halogen atoms

and/or straight-chain or branched alkoxy or alkylthio having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkoxy or halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 9 identical or different halogenatoms

and/or respectively doubly attached alkylene or dioxyalkylene having ineach case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen and/or straight-chain or branched alkyl having 1to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;

The invention in particular provides compounds of the formula (I) inwhich

A represents a single bond or represents methylene, 1,1-ethylene,1,2-ethylene, 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-,2,2-, 2,3-butylene or 1,1-, 1,2- or 1,3-(2-methyl-propylene), each ofwhich is optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, cyano andmethoxy,

Q represents oxygen or sulphur,

R¹ represents respectively optionally mono- to trisubstitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, phenyl, naphthyl,furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl,isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl,quinolyl, pyrimidyl, pyridazinyl, pyrazinyl, oxiranyl, oxetanyl,tetrahydrofuryl, perhydropyranyl, pyrrolidinyl, piperidinyl ormorpholinyl, the possible substituents preferably being selected fromthe list below:

fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl,carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinylor trifluoromethylsulphonyl, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethylamino, acetyl, propionyl,acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy,ethylsulphonyloxy, hydroxyiminomethyl, hydroxyiminoethyl,methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl orethoxyiminoethyl;

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- and i-propyl;

cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

phenyl, benzyl, phenoxy, benzyloxy, each of which is optionallysubstituted by the abovementioned substituents;

R² represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl or represents optionally substituted phenyl, the substituentsbeing selected from the abovementioned list for R¹,

R² and R³ join with the linking nitrogen atom to form an optionallymethyl-, ethyl-, methoxy- or ethoxy-substituted pyrrolidine, piperidineor morpholine ring,

R³ and R⁴ are identical or different and each represent hydrogen orrepresent methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,

R⁵ represents respectively optionally mono- to trisubstitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, phenyl, naphthyl,furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl,isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl,quinolyl, pyrimidyl, pyridazinyl, pyrazinyl, oxiranyl, oxetanyl,tetrahydrofuryl, perhydropyranyl, pyrrolidinyl, piperidinyl ormorpholinyl, the possible substituents preferably being selected fromthe list below:

fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl,carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino,dimethylamino, diethylamino, acetyl, propionyl, acetyloxy,methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl,ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl;

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- and i-propyl;

cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Particular preference is given to compounds of the formula (I) in which

A represents a single bond or represents methylene, 1,1-ethylene,1,2-ethylene, 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-,2,2-, 2,3-butylene or 1,1-, 1,2- or 1,3-(2-methyl-propylene), each ofwhich is optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, cyano andmethoxy,

Q represents oxygen or sulphur,

R¹ represents respectively optionally mono- to hexasubstitutedcyclobutyl, cyclopentyl or cyclohexyl, preferred substituents beingthose listed below;

represents respectively optionally mono- to trisubstituted phenyl,naphthyl, furyl, benzofuranyl, thienyl, benzothienyl, pyridyl, quinolyl,tetrahydrofuryl or perhydropyranyl, the possible substituents preferablybeing selected from the list below:

fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy,ethoxy, n- or i-propoxy, =methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl,trifluoromethylsulphonyl, acetyl, propionyl, acetyloxy, methoxycarbonyl,ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl,ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl;

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- and i-propyl; cyclopropyl,cyclopentyl, cyclohexyl; phenyl, phenoxy, benzyloxy, each of which isoptionally substituted by the abovementioned substituents;

R² represents hydrogen, methyl, ethyl, n- or i-propyl or representsoptionally methyl-, ethyl-, chlorine-, fluorine-, methoxy-, ethoxy- orhalogenomethoxy-substituted phenyl,

R³ represents hydrogen, methyl, ethyl, n- or i-propyl,

R² and R³ join with the linking nitrogen atom to form an optionallymethyl-substituted pyrrolidine, piperidine or morpholine ring,

R⁴ represents hydrogen, represents methyl or represents ethyl,

R⁵ represents respectively optionally mono- to hexasubstitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, preferredsubstituents being those listed below;

represents respectively optionally mono- to trisubstituted phenyl,naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl,oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl,thiadiazolyl, pyridyl, quinolyl, pyrimidyl, pyridazinyl, pyrazinyl,oxiranyl, oxetanyl, tetrahydrofuryl, perhydropyranyl, pyrrolidinyl,piperidinyl or morpholinyl, the possible substituents preferably beingselected from the list below:

fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl,carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino,dimethylamino, diethylamino, acetyl, propionyl, acetyloxy,methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl,ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl;

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- and i-propyl;

cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

A very particularly preferred group of compounds according to theinvention is formed by those compounds of the formula (I) in which

A represents a single bond or represents methylene, 1,1-ethylene,1,2-ethylene, 1,1-propylene, 1,2-propylene, 1,3-propylene or2,2-propylene,

Q represents oxygen,

R¹ represents phenyl, thienyl or furanyl, each of which is optionallymono- or disubstituted by bromine, chlorine, fluorine, nitro,methylsulphonyl, phenyl, phenyloxy, benzyloxy, cyclopropyl, cyclohexyl,methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl,n-heptyl, methoxy, ethoxy, trifluoromethyl and/or methylthio orrepresents phenyl which is substituted by 3,4methylene- andethylenedioxo, propane- 1,3-diyl and butane-1,4diyl, each of which isoptionally substituted by fluorine or represents naphthyl, benzofuranylor benzothienyl,

R² represents hydrogen, methyl, ethyl or represents phenyl which issubstituted by methoxy which is optionally substituted by methyl,chlorine, methoxy or fluorine,

R³ represents hydrogen, methyl or ethyl,

R² and R³ join with the linking nitrogen atom to form a pyrrolidine,piperidine or morpholine ring,

R⁴ represents hydrogen or methyl,

R⁵ represents cyclohexyl or optionally mono- to trisubstituted phenyl,thienyl, furyl, benzofuryl, benzothienyl, pyridyl, pyrimidyl, naphthyl,quinolyl, the possible substituents preferably being selected from thelist below:

fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl,carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino,dimethylamino, diethylamino, acetyl, propionyl, acetyloxy,methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl,ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl,

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- and i-propyl.

Of very particular interest are compounds of the formula (I) in whichthe radical R¹ represents unsubstituted phenyl or phenyl which issubstituted in position 3 and/or 4, or represents unsubstituted furanylor thienyl or furanyl or thienyl which is substituted in position 4and/or 5, the substituents being selected from the abovementioned group,in particular chlorine, bromine, fluorine, nitro, methylsulphonyl,phenyl, phenoxy, benzyloxy, cyclopropyl, cyclohexyl, methyl, ethyl, n-,i-propyl, n-, i-, -, t-butyl, n- pentyl, n-hexyl, n-heptyl, methoxy,ethoxy, methylthio and trifluoromethyl, or phenyl which is substitutedby 3,4-methylene- and ethylenedioxo, propane-1,3-diyl andbutane-1,4-diyl, each of which is optionally substituted by fluorine, ornaphthyl, benzofuranyl or benzothienyl.

Particular preference is also given to compounds of the formula (I) inwhich R⁵ represents phenyl which is substituted by methoxy in positions3 and 4.

The abovementioned general or preferred radical definitions apply bothto the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case forpreparation.

These radical definitions can be combined with each other as desired,that is to say combinations between the ranges stated for preferredcompounds are also possible.

Specific preferred compounds are listed in the tables below:

                  TABLE 1                                                         ______________________________________                                        (Ia)                                                                          1 #STR2##                                                                     Compound No.      R.sup.6                                                     ______________________________________                                        Ia-1              hydrogen                                                    Ia-2              4-chloro                                                    Ia-3              4-fluoro                                                    Ia-4              4-bromo                                                     Ia-5              4-methyl                                                    Ia-6              4-ethyl                                                     Ia-7              4-iso-propyl                                                Ia-8              4-n-propyl                                                  Ia-9              4-n-butyl                                                   Ia-10             4-iso-butyl                                                 Ia-11             4-tert-butyl                                                Ia-12             4-sec-butyl                                                 Ia-13             4-methoxy                                                   Ia-14             4-ethoxy                                                    Ia-15             4-methylthio                                                Ia-16             4-trifluoromethyl                                           Ia-17             3-chloro                                                    Ia-18             3-fluoro                                                    Ia-19             3-bromo                                                     Ia-20             3-methyl                                                    Ia-21             3-ethyl                                                     Ia-22             3-iso-propyl                                                Ia-23             3-n-propyl                                                  Ia-24             3-n-butyl                                                   Ia-25             3-iso-butyl                                                 Ia-26             3-tert-butyl                                                Ia-27             3-sec-butyl                                                 Ia-28             3-methoxy                                                   Ia-29             3-ethoxy                                                    Ia-30             3-methylthio                                                Ia-31             3-trifluoromethyl                                           Ia-32             3,4-dichloro                                                Ia-33             3,4-difluoro                                                Ia-34             3,4-dibromo                                                 Ia-35             3,4-dimethyl                                                Ia-36             3,4-diethyl                                                 Ia-37             3,4-OCH.sub.2 O                                             Ia-38             3,4-OCH.sub.2 CH.sub.2 O                                    Ia-39             3,4-OCF.sub.2 O                                             Ia-40             3,4-OCF.sub.2 CF.sub.2 O                                    Ia-41             3,4-(CH.sub.2).sub.3                                        Ia-42             3,4-(CH.sub.2).sub.4                                        Ia-43             3,4-di-methoxy                                              Ia-44             3,4-diethoxy                                                Ia-45             3,4-dimethylthio                                            Ia-46             3,4-di-trifluoromethyl                                      Ia-47             3-chloro, 4-methyl                                          Ia-48             4-chloro, 3-methyl                                          Ia-49             3-chloro, 4-methoxy                                         Ia-50             4-chloro, 3-methoxy                                         Ia-51             3-chloro, 4-ethyl                                           Ia-52             4-chloro, 3-ethyl                                           Ia-53             3-methoxy, 4-ethoxy                                         Ia-54             4-methoxy, 3 ethoxy                                         Ia-55             3-methyl, 4-methoxy                                         Ia-56             4-methyl, 3-methoxy                                         Ia-57             3-methyl, 4-ethyl                                           Ia-58             4-methyl, 3-ethyl                                           Ia-59             3-methoxy, 4-ethyl                                          Ia-60             4-methoxy, 3-ethyl                                          Ia-61             4-nitro                                                     Ia-62             4-methylsulphonyl                                           Ia-63             4-phenoxy                                                   Ia-64             4-phenyl                                                    Ia-65             4-benzyloxy                                                 Ia-66             4-pentyl                                                    Ia-67             4-hexyl                                                     Ia-68             4-heptyl                                                    Ia-69             4-cyclopropyl                                               Ia-70             4-cyclohexyl                                                ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                        (Ib)                                                                          2 #STR3##                                                                     Compound No.      R.sup.6                                                     ______________________________________                                        Ib-1              hydrogen                                                    Ib-2              4-chloro                                                    Ib-3              4-fluoro                                                    Ib-4              4-bromo                                                     Ib-5              4-methyl                                                    Ib-6              4-ethyl                                                     Ib-7              4-iso-propyl                                                Ib-8              4-n-propyl                                                  Ib-9              4-n-butyl                                                   Ib-10             4-iso-butyl                                                 Ib-11             4-tert-butyl                                                Ib-12             4-sec-butyl                                                 Ib-13             4-methoxy                                                   Ib-14             4-ethoxy                                                    Ib-15             4-methylthio                                                Ib-16             4-trifluoromethyl                                           Ib-17             5-chloro                                                    Ib-18             5-fluoro                                                    Ib-19             5-bromo                                                     Ib-20             5-methyl                                                    Ib-21             5-ethyl                                                     Ib-22             5-iso-propyl                                                Ib-23             5-n-propyl                                                  Ib-24             5-n-butyl                                                   Ib-25             5-iso-butyl                                                 Ib-26             5-sec-butyl                                                 Ib-27             5-tert-butyl                                                Ib-28             5-methoxy                                                   Ib-29             5-ethoxy                                                    Ib-30             5-methylthio                                                Ib-31             5-trifluoromethyl                                           Ib-32             4,5-dichloro                                                Ib-33             4,5-difluoro                                                Ib-34             4,5-dibromo                                                 Ib-35             4,5-dimethyl                                                Ib-36             4,5-diethyl                                                 Ib-37             4,5-di-methoxy                                              Ib-38             4,5-di-trifluormethyl                                       Ib-39             4-chloro, 5-methyl                                          Ib-40             5-chloro, 4-methyl                                          ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                                                      (Ic)                                            1 #STR4##                                                                     Compound No.      R.sup.6                                                     ______________________________________                                        Ic-1              hydrogen                                                    Ic-2              4-chloro                                                    Ic-3              4-fluoro                                                    Ic-4              4-bromo                                                     Ic-5              4-methyl                                                    Ic-6              4-ethyl                                                     Ic-7              4-iso-propyl                                                Ic-8              4-n-propyl                                                  Ic-9              4-n-butyl                                                   Ic-10             4-iso-butyl                                                 Ic-11             4-tert-butyl                                                Ic-12             4-sec-butyl                                                 Ic-13             4-methoxy                                                   Ic-14             4-ethoxy                                                    Ic-15             4-methylthio                                                Ic-16             4-trifluoromethyl                                           Ic-17             5-chloro                                                    Ic-18             5-fluoro                                                    Ic-19             5-bromo                                                     Ic-20             5-methyl                                                    Ic-21             5-ethyl                                                     Ic-22             5-iso-propyl                                                Ic-23             5-n-propyl                                                  Ic-24             5-n-butyl                                                   Ic-25             5-iso-butyl                                                 Ic-26             5-sec-butyl                                                 Ic-27             5-tert-butyl                                                Ic-28             5-methoxy                                                   Ic-29             5-ethoxy                                                    Ic-30             5-methylthio                                                Ic-31             5-trifluoromethyl                                           Ic-32             4,5-dichloro                                                Ic-33             4,5-difluoro                                                Ic-34             4,5-dibromo                                                 Ic-35             4,5-dimethyl                                                Ic-36             4,5-diethyl                                                 Ic-37             4,5-di-methoxy                                              Ic-38             4,5-di-trifluoromethyl                                      Ic-39             4-chloro, 5-methyl                                          Ic-40             5-chloro, 4-methyl                                          ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                                                      (Id)                                            2 #STR5##                                                                     Compound No.        R.sup.1                                                   ______________________________________                                        Id-1                2-naphthyl                                                I d-2               2-benzofuranyl                                            Id-3                2-benzothienyl                                            ______________________________________                                    

Table 5

Compounds Ia-1 to Id-3 corresponding to the formulae Ia, Ib, Ic and Idwhere the 3,4-dimethoxyphenyl group (generally denoted R⁵) has beenreplaced by a phenyl radical carrying the substituents reported as R⁶for the compounds Ia-1 to Ia-70.

Table 6

Compounds Ia-1 to Id-3 corresponding to the formulae Ia, Ib, Ic and Idwhere the 3,4-dimethoxyphenyl group (generally denoted R⁵) has beenreplaced by one of the following trisubstituted phenyl radicals:

substituents: 3,4,5-trimethoxy; 3,4,5-trichloro; 3,4,5-trimethyl.

Furthermore, it has been found that the novel hydrazonoacetamides of thegeneral formula (I) are obtained when carboxylic acid derivatives of thegeneral formula (II) ##STR6## in which R², R², R³ and Q are each asdefined above and

T represents hydroxyl, halogen or alkoxy are reacted with an amine ofthe general formula (III) ##STR7## in which R⁴, R⁵ and A are each asdefined above

or with a hydrogen halide thereof

if appropriate in the presence of an acid acceptor, if appropriate inthe presence of a condensing agent and if appropriate in the presence ofa diluent.

Formula (II) provides a general definition of the carboxylic acidderivatives required as starting materials for carrying out the processaccording to the invention. In this formula (II), (Q, R¹, R² and R³)each preferably have in particular those meanings which have alreadybeen indicated in connection with the description of the compounds ofthe formula (I) according to the invention as preferred or asparticularly preferred for (Q, R¹, R² and R³); T preferably representsalkoxy having 1 to 4 carbon atoms, in particular represents methoxy orethoxy, represents hydroxyl or chlorine.

The starting materials of the formula (II) are known and/or can beprepared by known processes (cf. J. Heterocycl. Chem. (1990), 27(3),487-95), Farmaco, Ed. Sci. (1980), 35(5), 394-404, Justus Liebigs Ann.Chem. (1969), 722, 38-44, Justus Liebigs Ann. Chem. (1969), 722, 29-37).

Formula (III) provides a general definition of the amines further to beused as starting materials.

The starting materials of the formula (III) are known organic chemicalsfor synthesis and/or can be prepared by methods known per se.

If appropriate, the process according to the invention is carried out inthe presence of a suitable acid acceptor. Suitable acid acceptors areall conventional inorganic or organic bases. These include, for example,alkaline earth metal or alkali metal hydrides, hydroxides, amides,alkoxides, acetates, carbonates or bicarbonates, such as, for example,sodium hydride, sodium amide, sodium methoxide, sodium ethoxide,potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammoniumhydroxide, sodium acetate, potassium acetate, calcium acetate, ammoniumacetate, sodium carbonate, potassium carbonate, potassium bicarbonate,sodium bicarbonate or ammonium carbonate, and tertiary amines, such astrimethylamine, triethylamine, tributylamine, N,N-dimethylanilin,N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine,N,N-dimethylaminopyridine, diazabicyclooctane (DABCO),triazabicyclononene (DBN) or diazabicycloundecene (DBU).

If appropriate, the process according to the invention is carried out inthe presence of a suitable condensing agent. Suitable condensing agentsare all condensing agents which are conventionally used for suchamidation reactions. Examples include acid halide formers such asphosgene, phosphorus tribromide, phosphorus trichloride, phosphoruspentachloride, phosphorus oxychloride or thionyl chloride; anhydrideformers such as ethyl chloroformate, methyl chloroformate ormethanesulphonyl chloride; carbodiimides, such asN,N'-dicyclohexyl-carbodiimide (DCC), or other conventional condensingagents, such as phosphorus pentoxide, polyphosphoric acid,N,N'-carbonyldiimidazol, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline(EEDQ) or triphenylphosphine/carbon tetrachloride.

If appropriate, the process according to the invention is carried out inthe presence of a diluent. Suitable diluents for carrying out theprocess according to the invention are water and organic solvents. Theseinclude in particular aliphatic, alicyclic or aromatic, optionallyhalogenated hydrocarbons, such as, for example, benzine, benzene,toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether,hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride;ethers, such as diethyl ether, diisopropyl ether, dioxan,tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycoldiethyl ether; ketones, such as acetone, butanone or methyl isobutylketone; nitriles, such as acetonitrile, propionitrile or benzonitrile;amides, such as N,N-dimethylformamide, N,N-dimethylacetamide,N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorictriamide; esters such as methyl acetate or ethyl acetate, sulphoxides,such as dimethyl sulphoxide, alcohols, such as methanol, ethanol, n- ori-propanol, ethylene glycol, ethylene glycol monomethyl ether, ethyleneglycol monoethyl ether, diethylene glycol monomethyl ether, diethyleneglycol monoethyl ether, their mixtures with water or pure water.

When carrying out the process according to the invention, the reactiontemperatures may be varied within a relatively wide range. In general,temperatures between -20° C. and +200° C., preferably temperaturesbetween 0° C. and 150° C., are employed.

In the practice of the process according to the invention, generally 1to 5 mol, preferably 1.0 to 2.5 mol, of amine are employed per mole ofcarboxylic acid derivative of the formula (II).

The reaction is carried out and reaction products are worked up andisolated according to known processes (cf. the Preparation Examples).

If appropriate, the process according to the invention is carried out inthe presence of a catalyst. Examples include 4-dimethylaminopyridine,1-hydroxy-benzotriazole and dimethylformamide.

When carrying out the process according to the invention, the reactiontemperatures may be varied within a relatively wide range. In general,temperatures between -78° C. and +120° C., preferably temperaturesbetween -60° C. and +25° C., are employed.

In the practice of the process according to the invention for preparingthe compounds of the formula (I), generally 0.5 to 5 mol, preferablyequimolar amounts, of amine of the formula (III) are employed per moleof the hydrazonoacetic acid derivative of the formula (II).

The reaction is carried out and the reaction products are worked up andisolated according to known processes (cf. the Preparation Examples).

The process according to the invention may also be carried out as atwo-step process. For this purpose, the hydrazonoacetic acid derivativesof general formula (II) are initially converted into an activated formand reacted with the amines of the general formula (III) in a subsequentstep to give the compounds of the general formula (I) according to theinvention.

Suitable activated forms of the hydrazonoacetic acid derivatives of theformula (II) are all carboxy-activated derivatives, such as, forexample, acyl halides, preferably acyl chlorides, acyl azides, furthersymmetric and mixed anhydrides, such as, for example, the mixed0-alkylcarbonic anhydrides, furthermore activated esters, such as, forexample, p-nitrophenyl esters or N-hydroxysuccinimide esters and adductswith condensing agents, such as, for example, dicyclohexylcarbodiimideor activated forms of the amino acids prepared in situ.

The active compounds according to the invention have potent microbicidalactivity and are employed in practice for controlling undesirablemicroorganisms. The active compounds are suitable for use as cropprotection agents, in particular as fungicides.

Fungicides are employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Some pathogens causing fungal diseases which come under the genericnames listed above may be mentioned as examples, but not by way oflimitation:

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Peronospora species, such as, for example, Peronospora pisi orPeronospora brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres orPyrenophora graminea (conidial form: Drechslera, synonym:Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidial form: Drechslera, synonym: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae;

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of aerial parts of plants, of propagation stock and seeds, andof the soil.

The active compounds according to the invention can be employedparticularly successfully for controlling diseases in viticulture,fruit-growing and vegetable-growing, for example against Plasmoparaspecies and Phytophthora species.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted, if desired, to the customaryformulations, such as solutions, emulsions, suspensions, powders, foams,pastes, granules, aerosols and microencapsulations in polymericsubstances and in coating compositions for seeds, and ULV cold and warmfogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. In the case of the use of water as an extender, organicsolvents can, for example, also be used as auxiliary solvents.Essentially, the following are suitable as liquid solvents: aromaticssuch as xylene, toluene or alkylnaphthalenes, chlorinated aromatics orchlorinated aliphatic hydrocarbons such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons such ascyclohexane or paraffins, for example petroleum fractions, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water; liquefied gaseous extenders or carriers areto be understood as meaning liquids which are gaseous at ambienttemperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, or else butane, propane,nitrogen and carbon dioxide; suitable solid carriers are: for example,ground natural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example, crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample, nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates,or else protein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or,in their formulations, also as a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides in order thus, forexample, to widen the spectrum of action or to prevent development ofresistance.

In many cases, synergistic effects are achieved.

Examples of possible co-components for mixtures are the followingcompounds:

Fungicides:

2-aminobutane; 2-anilino4-methyl-6-cyclopropyl-pyrimidine;2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxy-phenyl)-acetamide;8-hydroxyquinoline sulphate; methyl(E)-2-{2-[6(2-cyanophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate; methyl(E)-methoximino[alpha-(o-tolyloxy)-o-tolyl]acetate; 2-phenylphenol(OPP), aldimorph, ampropylfos, anilazine, azaconazole,

benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate,

calcium polysulphide, captafol, captan, carbendazim, carboxin,quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate,cufraneb, cymoxanil, cyproconazole, cyprofuram,

dichlorophen, diclobutrazol, diclofluanid, diclomezine, dicloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine,drazoxolon,

edifenphos, epoxyconazole, ethirimol, etridiazole,

fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet,fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazol,

imazalil, imibenconazole, iminoctadine, iprobenfos (IBP), iprodione,isoprothiolane,

kasugamycin, copper preparations such as: copper hydroxide, coppernaphthenate, copper oxychloride, copper sulphate, copper oxide,oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl,metconazole,

methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxycarboxin,

pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin,polyoxin, probenazole, prochloraz, procymidone, propamocarb,propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil,pyroquilon,

quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole,thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid,triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole,tridemorph, triflumizole, triforine, triticonazole,

validamycin A, vinclozolin,

zineb, ziram.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin,

Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap,betacyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb,buprofezin, butocarboxin, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,CGA 157419, CGA 184699, chloethocarb, chlorethoxyfos, chloretoxyfos,chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifosM, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etofenprox, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate,

fipronil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron,flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox,furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivemectin,

lamda-cyhalothrin, lufenuron,

malathion, mecarbam, mervinphos, mesulfenfos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamdon, phoxim, pirimicarb, pirimiphos M, primiphos A,profenofos, profenophos, promecarb, propaphos, propoxur, prothiofos,prothiophos, prothoate, pymetrozin, pyrachlophos, pyraclofos,pyraclophos, pyradaphenthion, pyresmethrin, pyrethrum, pyridaben,pyrimidifen, pyriproxifen,

quinalphos,

RH 5992,

salithion, sebufos, silafluofen, sulfotep, sulprofos,

tebufenozid, tebufenpyrad, tebupirirmphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathene, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamidothion, XMC, xylylcarb, zetamethrin.

It is also possible to mix the active compounds according to theinvention with other known active compounds, such as herbicides, orfertilizers and growth regulators.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. They are used in the customary manner, for example bywetting, spraying, atomizing, spreading, dusting, foaming, brushing onand the like. It is further possible to apply the active compounds bythe ultra-low volume method or to inject the active compoundformulation, or the active compound itself, into the soil. The seed ofthe plants can also be treated.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range. They are, ingeneral, between 1 and 0.0001% by weight, preferably between 0.5 and0.001% by weight.

In the treatment of seed, amounts of active compound of from 0.001 to 50g, preferably 0.01 to 10 g, are generally required per kilogram of seed.

In the treatment of the soil, active compound concentrations of from0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight,are required at the treatment site.

PREPARATION EXAMPLE 1 ##STR8##

0.8 g (3.4 mmol) of ethyl2-N,N-dimethyl-hydrazono-2-(4-methylphenyl)-acetate is initially chargedin 10 ml of methanol and, at room temperature, 0.6 g (3.4 mmol) of2-(3,4-dimethoxyphenyl)-ethylamine and 1.2 g (6.8 mmol) of 30% strengthmethanolic sodium methoxide solution are added in succession.

The mixture is stirred at 65° C. for 20 h, the solvent is then distilledoff and the residue is taken up in methylene chloride and washedsuccessively with water, dilute hydrochloric acid and water and driedover sodium sulphate. The solvent is distilled off and the crude productis chromatographed over silica gel using petroleum ether/ethyl acetate(10:1).

0.3 g (25% of theory) ofN-[2-(3,4-dimethoxyphenyl)-ethyl]-2-N,N-dimethylhydrazono-2-(4-methylphenyl)acetamideis obtained.

¹ H NMR (CDCl₃, TMS): δ=2.70 (S, 6H); 3.87 (S, 6H).

By the method of Example 1, and according to the procedures of thegeneral description of the process, the compounds of the formula (Id)listed in Table 7 below are obtained: ##STR9##

                  TABLE 7                                                         ______________________________________                                        No.  R.sup.1   R.sup.2   R.sup.3                                                                             E/Z  phys. const.                              ______________________________________                                        2    4-CH.sub.3                                                                              Ph        H     E/Z  log p: 3.44/4.22                          3    4-CH.sub.3                                                                              4-CF.sub.3 O-Ph                                                                         H     E/Z  log p: 4.16/4.92                          4    4-CH.sub.3                                                                              CH.sub.3  CH.sub.3                                                                            Z    log p: 2.94                               5    4-CH.sub.3                                                                              CH.sub.3  CH.sub.3                                                                            E    log p: 2.61                               6    4-Br      CH.sub.3  CH.sub.3                                                                            E/Z  log p: 2.78/3.14                          7    4-C.sub.2 H.sub.3                                                                       CH.sub.3  CH.sub.3                                                                            E/Z  log p: 2.89/3.22                          8    4-CH.sub.3                                                                              4-CF.sub.3 OPh                                                                          H     E    log p: 4.93                               9    4-CH.sub.3                                                                              4-CF.sub.3 OPh                                                                          H     Z    log p: 4.16                               10   4-Br      Ph        H     E/Z  log p: 3.64/4.50                          11   4-C.sub.2 H.sub.5                                                                       Ph        H     E/Z  log p: 3.81/4.61                          12   4-C.sub.2 H.sub.5                                                                       CH.sub.3  H     E/Z  log p: 3.15/3.42                          13   4-Cl      CH.sub.3  CH.sub.3                                                                            E/Z  log p: 2.66/3.04                          14   4-Br      CH.sub.3  CH.sub.3                                                                            E    log p: 2.77                               15   4-Br      CH.sub.3  CH.sub.3                                                                            Z    log p: 3.14                               16   3,4-(CH.sub.2).sub.4                                                                    CH.sub.3  CH.sub.3                                                                            E/Z  log p: 2.84/3.19                          17   3,4-(CH.sub.2).sub.4                                                                    CH.sub.3  H     E/Z  log p: 2.75/3.13                          18   3,4-(CH.sub.2).sub.4                                                                    Ph        H     E/Z  log p: 4.16/5.01                          19   4-CH.sub.3                                                                              Ph        H     Z    log p: 4.21                               20   3,4-(CH.sub.2).sub.3                                                                    CH.sub.3  H     E/Z  log p: 3.19/3.47                          21   3,4-(CH.sub.2).sub.3                                                                    CH.sub.3  CH.sub.3                                                                            E/Z  log p: 2.43/3.36                          22   3,4-(CH.sub.2).sub.3                                                                    Ph        H     E/Z  log p: 3.89/4.72                          23   4-Br      CH.sub.3  H     E/Z  log p: 2.88/3.42                          24   4-Cl      Ph        H     E/Z  log p: 3.54/4.38                          25   4-Cl      CH.sub.3  CH.sub.3                                                                            Z    log p: 3.03                               26   4-C.sub.2 H.sub.5                                                                       CH.sub.3  CH.sub.3                                                                            Z    log p: 3.32                               27   3,4-(CH.sub.2).sub.3                                                                    CH.sub.3  CH.sub.3                                                                            Z    log p: 3.36                               28   4-Cl      Ph        H     Z    log p: 4.38                               29   4-Cl      (CH.sub.2).sub.5                                                                            E/Z  log p: 4.16/5.01                            30   3,4-(CH.sub.2).sub.4                                                                    CH.sub.3  CH.sub.3                                                                            Z    log p: 3.19                               31   3,4-(CH.sub.2).sub.4                                                                    CH.sub.3  H     Z    log p: 3.73                               32   3,4-(CH.sub.2).sub.3                                                                    Ph        H     Z    log p: 4.72                               33   4-CH.sub.3                                                                              (CH.sub.2).sub.5                                                                            E/Z  log p: 3.66/3.84                            34   4-Br      Ph        H     Z    log p: 4.48                               35   4-Br      Ph        H     E    log p: 3.60                               36   3,4-(CH.sub.2).sub.4                                                                    CH.sub.3  H     E    log p: 2.75                               37   4-Br      (CH.sub.2).sub.5                                                                            E/Z  log p: 3.56/4.06                            38   4-C.sub.2 H.sub.5                                                                       (CH.sub.2).sub.5                                                                            E/Z  log p: 3.11/4.25                            39   3,4-(CH.sub.2).sub.3                                                                    (CH.sub.2).sub.5                                                                            E/Z  log p: 3.05/4.31                            40   3,4-(CH.sub.2).sub.4                                                                    (CH.sub.2).sub.5                                                                            Z    log p: 4.65                                 41   4-Br      (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                          E/Z  log p: 2.72/2.91                            42   4-Cl      (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                          E/Z  log p: 2.62/2.80                            43   3,4-(CH.sub.2).sub.4                                                                    (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                          E/Z  log p: 3.25/3.36                            44   3,4-(CH.sub.2).sub.3                                                                    (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                          E/Z  log p: 2.93/3.07                            45   3,4-(CH.sub.2).sub.3                                                                    (CH.sub.2).sub.4                                                                            E/Z  log p: 2.92/3.15                            46   3,4-(CH.sub.2).sub.4                                                                    (CH.sub.2).sub.4                                                                            E/Z  log p: 3.25/3.50                            47   3,4-(CH.sub.2).sub.4                                                                    (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                          Z    log p: 3.36                                 48   3,4-(CH.sub.2).sub.3                                                                    (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                          Z    log p: 3.07                                 ______________________________________                                    

Example A

Phytophthora test (tomato)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the. concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound. After the spray coating has dried on,the plants are inoculated with an aqueous suspension of spores ofPhytophthora infestans.

The plants are placed in an incubation cabinet at a relative atmospherichumidity of 100% and approximately 20° C.

Evaluation is carried out 3 days after the inoculation.

In this test, the compounds 1, 4, 14, 16, 17, 20, 29 and 31 according tothe invention exhibit, at an active compound concentration of 100 ppm inthe spray liquor, an efficacy of more than 80%.

Example B

Plasmopara test (vine)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound. After the spray coating has dried on,the plants are inoculated with an aqueous suspension of spores ofPlasmopara viticola and then remain in a humidity chamber at 20 to 22°C. and 100% relative atmospheric humidity for 1 day. Subsequently, theplants are kept in a greenhouse at 21° C. and 90% relative atmospherichumidity for 5 days. The plants are then moistened and kept for 1 day ina humidity chamber.

Evaluation is carried out 6 days after the inoculation.

In this test, the compounds 1, 4, 14, 16, 17, 20, 29 and 31 according tothe invention exhibit, at an active compound concentration of 100 ppm inthe spray liquor, an efficacy of more than 80%.

We claim:
 1. A compound of the formula (I) ##STR10## in which Arepresents optionally substituted alkylene,Q represents oxygen orsulphur, R¹ represents respectively optionally substituted cycloalkyl,cycloalkenyl, or aryl, R² represents hydrogewn or respectivelyoptionally substituted alkyl, cycloalkyl, cycloalkenyl, or aryl, R³ andR⁴ are identical or different and each represents hydrogen orrespectively optionally substituted alkyl or cycloalkyl, R⁵ representsrespectively optionally substituted cycloalkyl, cycloalkenyl, or aryl.2. A compound of the formula (I) according to claim 1 in whichArepresents alkylene having 1 to 6 carbon atoms which is optionally mono-or polysubstituted by identical or different substituents, thesubstituents being selected from the list below:halogen, cyano, nitro,amino, hydroxyl, formyl, carboxy, carbamoyl, thiocarbamoyl; respectivelystraight-chain or branched alkoxy, alkylthio, alkylsulphinyl oralkylsulphonyl having in each case 1 to 6 carbon atoms; respectivelystraight-chain or branched alkenyl or alkenyloxy having in each case 2to 6 carbon atoms; respectively straight-chain or branchedhalogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl orhalogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to13 identical or different halogen atoms; respectively straight-chain orbranched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to6 carbon atoms and 1 to 13 identical or different halogen atoms;respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 6 carbonatoms in the individual alkyl moieties; cycloalkyl having 3 to 6 carbonatoms; and aryl which is optionally mono- or polysubstituted byidentical or different substituents from halogen, cyano and/orstraight-chain or branched alkyl having 1 to 4 carbon atoms; and/orstraight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 9 identical or different halogen atoms; and/or straight-chain orbranched alkoxy or alkylthio having 1 to 4 carbon atoms; and/orstraight-chain or branched halogenoalkoxy or halogenoalkylthio having 1to 4 carbon atoms and 1 to 9 identical or different halogen atoms;and/or respectively doubly attached alkylene or dioxyalkylene having ineach case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different substituents from halogenand/or straight-chain or branched alkyl having 1 to 4 carbon atomsand/or straight-chain or branched halogenoalkyl having 1 to 4 carbonatoms and 1 to 9 identical or different halogen atoms; Q representsoxygen or sulphur, R¹ represents aryl, cycloalkyl or cycloalkenyl having3 to 7 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different substituents, the substituentsbeing selected from the list below:halogen, cyano, nitro, amino,hydroxyl, formyl, carboxy, carbamoyl, thiocarbamoyl; respectivelystraight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl oralkylsulphonyl having in each case 1 to 6 carbon atoms; respectivelystraight-chain or branched alkenyl or alkenyloxy having in each case 2to 6 carbon atoms; respectively straight-chain or branchedhalogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinylor halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1to 13 identical or different halogen atoms; respectively straight-chainor branched halogenoalkenyl or halogenoalkenyloxy having in each case 2to 6 carbon atoms and 1 to 13 identical or different halogen atoms;respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 8 carbonatoms in the individual alkyl moieties; respectively doubly attachedalkylene or dioxyalkylene having in each case 1 to 6 carbon atoms, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of halogen andstraight-chain or branched alkyl having 1 to 4 carbon atoms andstraight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 9 identical or different halogen atoms; cycloalkyl having 3 to 6carbon atoms; and aryl, aryloxy, arylthio, arylalkyl, arylalkyloxy or,arylalkylthio, each of which is optionally mono or polysubstituted byidentical or different substituents from halogen, cyano and/orstraight-chain or branched alkyl having 1 to 4 carbon atoms; and/orstraight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 9 identical or different halogen atoms; and/or straight-chain orbranched alkoxy or alkylthio having 1 to 4 carbon atoms; and/orstraight-chain or branched halogenoalkoxy or halogenoalkylthio having 1to 4 carbon atoms and 1 to 9 identical or different halogen atoms;and/or respectively doubly attached alkylene or dioxyalkylene having ineach case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen and/or straight-chain or branched alkyl having 1to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms R²represents hydrogen or represents alkyl having 1 to 4 carbon atoms orcycloalkyl having 3 to 6 carbon atoms, each of which is optionally mono-or polysubstituted by identical or different substituents from the groupconsisting of halogen, cyano, hydroxyl, amino, C₁ -C₄ -alkoxy, C₁ -C₄-alkylthio, C₁ -C₄ -alkylsulphinyl and C₁ -C₄ -alkylsulphonyl (each ofwhich is optionally substituted by halogen) or represents optionallysubstituted phenyl, the substituents being selected from the list for R¹above, R³ and R⁴ are identical or different and each represent hydrogenor represent alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to6 carbon atoms, each of which is optionally mono- or polysubstituted byidentical or different substituents from the group consisting ofhalogen, cyano, hydroxyl, amino, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁-C₄ -alkylsulphinyl and C₁ -C₄ -alkylsulphonyl (each of which isoptionally substituted by halogen), R⁵ represents aryl, cycloalkyl orcycloalkenyl having 3 to 8 carbon atoms, each of which is optionallymono- or polysubstituted by identical or different substituents, thesubstituents being selected from the list below:halogen, cyano, nitro,amino, hydroxyl, formyl, carboxy, carbamoyl, thiocarbamoyl, respectivelystraight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl oralkylsulphonyl having in each case 1 to 6 carbon atoms; respectivelystraight-chain or branched alkenyl or alkenyloxy having in each case 2to 6 carbon atoms; respectively straight-chain or branchedhalogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinylor halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1to 13 identical or different halogen atoms; respectively straight-chainor branched halogenoalkenyl or halogenoalkenyloxy having in each case 2to 6 carbon atoms and 1 to 13 identical or different halogen atoms;respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 6 carbonatoms in the individual alkyl moieties; and respectively doubly attachedalkylene or dioxyalkylene having in each case 1 to 6 carbon atoms, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of halogen andstraight-chain or branched alkyl having 1 to 4 carbon atoms andstraight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 9 identical or different halogen atoms.
 3. A compound of theformula (I) according to claim 1 in whichA represents methylene,1,1-ethylene, 1,2-ethylene, 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-,1,2-, 1,3-, 1,4-, 2,2-, 2,3-butylene or 1,1-, 1,2- or1,3-(2-methyl-propylene), each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, cyano and methoxy, Q represents oxygenor sulphur, R¹ represents respectively optionally mono- totrisubstituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,phenyl or, naphthyl, the substituents being selected from the listbelow:fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl,formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinylor trifluoromethylsulphonyl, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethylamino, acetyl, propionyl,acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy,ethylsulphonyloxy, hydroxyiminomethyl, hydroxyiminoethyl,methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl orethoxyiminoethyl; respectively doubly attached trimethylene(propane-1,3-diyl), tetramethylene (butane-1,4diyl), methylenedioxy orethylenedioxy, each of which is optionally mono- or polysubstituted byidentical or different substituents from the group consisting offluorine, chlorine, methyl, trifluoromethyl, ethyl, n- and i-propyl;cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; phenyl, benzyl,phenoxy, benzyloxy, each of which is optionally substituted by theabovementioned substituents; R² represents hydrogen, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl or represents optionally substitutedphenyl, the substituents being selected from the abovementioned list forR¹, R³ and R⁴ are identical or different and each represent hydrogen orrepresent methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R⁵represents respectively optionally mono- to trisubstituted cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl, phenyl or, naphthyl, thesubstituents being selected from the list below:fluorine, chlorine,bromine, cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl,thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio,trifluoromethylsulphinyl or trifluoromethylsulphonyl, methylamino,ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl,propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl,methylsulphonyloxy, ethylsulphonyloxy, hydroxyiminomethyl,hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl,methoxyiminoethyl or ethoxyiminoethyl; respectively doubly attachedtrimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl),methylenedioxy or ethylenedioxy, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- andi-propyl; and cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
 4. Acompound of the formula (I) according to claim 1 in whichA representsmethylene, 1,1 -ethylene, 1,2-ethylene, 1,1-, 1,2-, 1,3- or2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4, 2,2-, 2,3-butylene or 1,1-, 1,2-or 1,3-(2-methyl-propylene), each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, cyano and methoxy, Q represents oxygenor sulphur, R¹ represents respectively optionally mono- tohexasubstituted cyclobutyl, cyclopentyl or cyclohexyl, the substituentsbeing those listed below;represents respectively optionally mono- totrisubstituted phenyl, or naphthyl, the substituents being selected fromthe list below: fluorine, chlorine, bromine, cyano, nitro, methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl,n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio,trifluoromethylsulphinyl, trifluoromethylsulphonyl, acetyl, propionyl,acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy,ethylsulphonyloxy, hydroxyiminomethyl, hydroxyiminoethyl,methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl orethoxyiminoethyl; and respectively doubly attached trimethylene(propane- 1,3-diyl), tetramethylene (butane-1,4-diyl), methylenedioxy orethylenedioxy, each of which is optionally mono- or polysubstituted byidentical or different substituents from the group consisting offluorine, chlorine, methyl, trifluoromethyl, ethyl, n- and i-propyl;cyclopropyl, cyclopentyl, cyclohexyl; phenyl, phenoxy, benzyloxy, eachof which is optionally substituted by the abovementioned substituents;R² represents hydrogen, methyl, ethyl, n- or i-propyl or representsoptionally methyl-, ethyl-, chlorine-, fluorine-, methoxy-, ethoxy- orhalogenomethoxy-substituted phenyl, R³ represents hydrogen, methyl,ethyl, n- or i-propyl, R⁴ represents hydrogen, represents methyl orrepresents ethyl, R⁵ represents respectively optionally mono- tohexasubstituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, thesubstituents being those listed below; orrepresents respectivelyoptionally mono- to trisubstituted phenyl, or naphthyl, the possiblesubstituents preferably being selected from the list below: fluorine,chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, carboxy,carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio,trifluoromethylsulphinyl or trifluoromethylsulphonyl, methylamino,ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl,propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl,methylsulphonyloxy, ethylsulphonyloxy, hydroxyiminomethyl,hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl,methoxyiminoethyl or ethoxyiminoethyl; respectively doubly attachedtrimethylene (propane-1,3diyl), tetramethylene (butane- 1,4diyl),methylenedioxy or ethylenedioxy, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- andi-propyl; and cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
 5. Acompound of the formula (I) according to claim 1 in whichA representsmethylene, 1,l-ethylene, 1,2-ethylene, 1,1-propylene, 1,2-propylene,1,3-propylene or 2,2-propylene, Q represents oxygen, R¹ representsphenyl, which is optionally mono- or disubstituted by bromine, chlorine,fluorine, nitro, methylsulphonyl, phenyl, phenyloxy, benzyloxy,cyclopropyl, cyclohexyl, methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, trifluoromethyland/or methylthio or represents phenyl which is substituted by3,4-methylene- and ethylenedioxo, propane-1,3-diyl and butane-1,4-diyl,each of which is optionally substituted by fluorine or representsnaphthyl, R² represents hydrogen, methyl, ethyl or represents phenylwhich is substituted by methoxy which is optionally substituted bymethyl, chlorine, methoxy or fluorine, R³ represents hydrogen, methyl orethyl, R⁴ represents hydrogen or methyl, R⁵ represents cyclohexyl oroptionally mono- to trisubstituted phenyl, or naphthyl, the substituentsbeing selected from the list below:fluorine, chlorine, bromine, cyano,nitro, amino, hydroxyl, formyl, carboxy, carbamoyl, thiocarbamoyl,methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy,n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinylor trifluoromethylsulphonyl, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethylamino, acetyl, propionyl,acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy,ethylsulphonyloxy, hydroxyiminomethyl, hydroxyiminoethyl,methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl orethoxyiminoethyl, and respectively doubly attached trimethylene(propane-1,3-diyl), tetramethylene (butane-1,4diyl), methylenedioxy orethylenedioxy, each of which is optionally mono- or polysubstituted byidentical or different substituents from the group consisting offluorine, chlorine, methyl, trifluoromethyl, ethyl, n- and i-propyl. 6.Process for preparing compounds of the formula ##STR11## in which Arepresents an optionally substituted alkylene,Q represents oxygen orsulphur, R¹ represents respectively optionally substituted cycloalkyl,cycloalkenyl, or aryl, R¹, R³ and R⁴ are identical or different and eachrepresent hydrogen or respectively optionally substituted alkyl, R⁵represents respectively optionally substituted cycloalkyl, cycloalkenyl,or aryl,characterized in that carboxylic acid derivatives of the generalformula (II) ##STR12## in which R², R², R³ and Q are each as definedabove and T represents hydroxyl, halogen or alkoxyare reacted with anamine of the general formula (III) ##STR13## in which R⁴, R⁵ and A areeach as defined above or with a hydrogen halide thereof optionally inthe presence of an acid acceptor, optionally in the presence of acondensing agent and optionally in the presence of a diluent.
 7. Apesticidal composition comprising a diluent and a pesticidally effectiveamount of a compound of the formula (I) ##STR14## in which A representsoptionally substituted alkylene,Q represents oxygen or sulphur, R¹represents respectively optionally substituted cycloalkyl, cycloalkenyl,aryl or heterocyclyl, R² represents hydrogen or respectively optionallysubstituted alkyl, cycloalkyl, cycloalkenyl, or aryl, R³ and R⁴ areidentical or different and each represents hydrogen or respectivelyoptionally substituted alkyl or cycloalkyl, R⁵ represents respectivelyoptionally substituted cycloalkyl, cycloalkenyl, or aryl.
 8. A methodfor controlling pests comprising administering to said pests and/ortheir habitat a pesticidally effective amount of a compound of theformula (I) ##STR15## in which A represents optionally substitutedalkylene,Q represents oxygen or sulphur, R¹ represents respectivelyoptionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl,R² represents hydrogen or respectively optionally substituted alkyl,cycloalkyl, cycloalkenyl, or aryl, R³ and R⁴ are identical or differentand each represents hydrogen or respectively optionally substitutedalkyl or cycloalkyl, R⁵ represents respectively optionally substitutedcycloalkyl, cycloalkenyl, or aryl.